Our interest in understanding the determinants of adolescent childbearing and how adolescent childbearing influences educational trajectories derive from a concern about the inverse relationship between educational outcomes and adolescent fertility. Through in-depth interviews with 118 women, we contrast the educational trajectories of adolescent and adult childbearers in urban neighborhoods in Paraguay and Peru. The findings suggest that adolescents who face obstacles that discourage academic achievement and high aspirations in life are also more likely to bear children.